5-Methoxyindoleacetic acid → 1-[(5-methoxy-1H-indol-3-yl)methylcarbonyl]-4-(4-nitrophenyl)-piperazine

HRID 393846

Reaction equation

HRID 393846 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][C:25]([OH:27])=O.[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)=[CH:33][CH:32]=1)([O-:30])=[O:29]>C1COCC1.CN(C=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:24][C:25]([N:40]1[CH2:41][CH2:42][N:37]([C:34]2[CH:33]=[CH:32][C:31]([N+:28]([O-:30])=[O:29])=[CH:36][CH:35]=2)[CH2:38][CH2:39]1)=[O:27]

Participants

6

Reactant 3

HCID 189865-Methoxyindoleacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 219187071-[(5-methoxy-1H-indol-3-yl)methylcarbonyl]-4-(4-nitrophenyl)-piperazineYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a 100 ml flask, 1.62 g (10 mmoles) of 1.1′-carbonyl-diimidazole is added to a solution of 2.05 g (10 mmoles) of 5-methoxyindole-3-acetic acid in 10 ml of THF. After one hour of agitation at ambient temperature, a solution of 1-(4-nitrophenyl)piperazine in 10 ml of DMF is added dropwise. Agitation is continued for 15 hours. The reaction medium is then concentrated under vacuum and the evaporation residue is precipitated from 50 ml of an ethyl acetate/water mixture (1/1). After filtration, the solid is rinsed successively with 50 ml of water, 50 ml of ethyl acetate and 50 ml of dichloromethane. After drying under vacuum, a yellow powder is obtained with a yield of 91%. Melting point: 239-240° C.

Workup

  1. waitAgitation is continued for 15 hours
  2. concentrationThe reaction medium is then concentrated under vacuum
  3. customthe evaporation residue is precipitated from 50 ml of an ethyl acetate/water mixture (1/1)
  4. filtrationAfter filtration
  5. washthe solid is rinsed successively with 50 ml of water, 50 ml of ethyl acetate and 50 ml of dichloromethane
  6. customAfter drying under vacuum
  7. customa yellow powder is obtained with a yield of 91%

Sources & evidence

ORD record
ord-85bddbea320546c6abf8f21b6ef7027c
Source dataset
uspto-grants-2004_10
Patent number
US06809088B2

Linked notes

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